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Sailing Trips Starting In October 2026 and 2027

Are you looking to embark on a sailing trip in October 2026 or 2027? Choose from 31 unique trip itineraries and 1,050 departures from the world's leading touring operators.
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31 Trips (1,050 Trip Departures)
8 Day Croatia Sailing Adventure: Dubrovnik to Split with Intrepid Travel
Cruise
 (1)

8 Days (7 Nights) Dubrovnik to Split
Operated By: Intrepid Travel
Departures: May 2026 to Oct 2027
Visit: Croatia
Exclusive Savings
From
US$1,698
Save 546
Per Person
View Trip
18 Day Sri Lanka with Maldives Cruise: Spice Gardens & Seasides with G Adventures
Tour + Cruise

18 Days Negombo to Male
Operated By: G Adventures
Departures: May 2026 to Dec 2027
Trip Styles: Small Group, 18-30's, Sailing
Visit: Sri Lanka, Maldives
Exclusive Savings
From
US$2,437
Save 812
Per Person
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8 Day Maldive Dhoni Cruise with Explore Worldwide
Cruise

8 Days (7 Nights) Male to Male
Operated By: Explore Worldwide
Departures: Apr 2026 to Dec 2027
Visit: Maldives
Exclusive Savings
From
US$2,080
Save 280
Per Person
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14 Day Essential India & Maldives Sailing with G Adventures
Tour + Cruise

14 Days Delhi to Male
Operated By: G Adventures
Departures: Jun 2026 to Dec 2027
Trip Styles: Adventure, Small Group, Sailing
Visit: India, Maldives
Exclusive Savings
From
US$2,249
Save 750
Per Person
View Trip
7 Day Amalfi Coast Sailing Adventure with Intrepid Travel
Cruise

7 Days (6 Nights) Naples to Procida
Operated By: Intrepid Travel
Departures: May 2026 to Oct 2027
Visit: Italy
Exclusive Savings
From
US$2,447
Save 510
Per Person
View Trip
7 Day Maldives Dhoni Explorer with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: May 2026 to Dec 2027
Visit: Maldives
Exclusive Savings
From
US$1,724
Save 657
Per Person
View Trip
7 Day Egypt: Ancient Wonders & Temples of the Nile with G Adventures
New ReleaseTour

7 Days Cairo to Luxor
Operated By: G Adventures
Departures: May 2026 to Jan 2028
Trip Styles: Adventure, Small Group, Sailing
Visit: Egypt
Exclusive Savings
From
US$2,804
Save 495
Per Person
View Trip
18 Day Bali & Beyond with TruTravels
New ReleaseTour + Cruise

18 Days Canggu to Labuan Bajo
Operated By: TruTravels
Departures: May 2026 to Nov 2027
Visit: Indonesia
Exclusive Savings
From
US$1,575
Save 675
Per Person
View Trip
8 Day Sail Greece: Mykonos to Santorini with Intrepid Travel
Cruise

8 Days (7 Nights) Mykonos to Santorini
Operated By: Intrepid Travel
Departures: May 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$1,553
Save 463
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operated By: G Adventures
Departures: Apr 2026 to Sep 2027
Visit: Croatia
Exclusive Savings
From
US$974
Save 975
Per Person
View Trip
8 Day Sailing Greece - Santorini to Mykonos with G Adventures
Cruise

8 Days (7 Nights) Santorini to Mykonos
Operated By: G Adventures
Departures: May 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$1,175
Save 504
Per Person
View Trip
8 Day Sail Maldives with Intrepid Travel
Cruise

8 Days (7 Nights) Male to Male
Operated By: Intrepid Travel
Departures: May 2026 to Dec 2027
Visit: Maldives
Exclusive Savings
From
US$2,763
Save 350
Per Person
View Trip
7 Day Sailing the Canary Islands with G Adventures
Cruise

7 Days (6 Nights) San Miguel de Abona to San Miguel de Abona
Operated By: G Adventures
Departures: Oct 2026 to Apr 2028
Visit: Spain
From
US$1,199
Per Person
View Trip
8 Day Croatia Sailing Adventure: Split to Dubrovnik with Intrepid Travel
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operated By: Intrepid Travel
Departures: May 2026 to Oct 2027
Visit: Croatia
Exclusive Savings
From
US$1,646
Save 656
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: May 2026 to Oct 2027
Visit: Croatia
Exclusive Savings
From
US$1,169
Save 780
Per Person
View Trip
8 Day Greece: Sail & Swim with Topdeck
New ReleaseCruise

8 Days (7 Nights) Athens to Athens
Operated By: Topdeck
Departures: May 2026 to Oct 2026
Visit: Greece
Exclusive Savings
From
US$2,412
Save 130
Per Person
View Trip
8 Day Sail Greece: Santorini to Mykonos with Intrepid Travel
Cruise

8 Days (7 Nights) Santorini to Mykonos
Operated By: Intrepid Travel
Departures: May 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$1,489
Save 504
Per Person
View Trip
6 Day Komodo & Flores Sail with Contiki
New ReleaseTour + Cruise

6 Days Sanur to Labuan Bajo
Operated By: Contiki
Departures: Jun 2026 to Oct 2026
Visit: Indonesia
Exclusive Savings
From
US$1,379
Save 138
Per Person
View Trip
7 Day Maldives Dhoni Cruise with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: May 2026 to Dec 2027
Visit: Maldives
Exclusive Savings
From
US$1,499
Save 500
Per Person
View Trip
14 Day Highlights of Sri Lanka with Maldive Dhoni Cruise (East Coast) with Explore Worldwide
Tour + Cruise

14 Days Negombo to Male
Operated By: Explore Worldwide
Departures: Aug 2026 to Oct 2027
Trip Styles: Adventure, Small Group, Sailing
Visit: Sri Lanka, Maldives
From
US$3,360
Per Person
View Trip
8 Day Montenegro Sailing with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operated By: G Adventures
Departures: Apr 2026 to Oct 2027
Visit: Montenegro, Croatia
Exclusive Savings
From
US$974
Save 975
Per Person
View Trip
26 Day Total Indonesia with TruTravels
New ReleaseTour + Cruise

26 Days Medan to Labuan Bajo
Operated By: TruTravels
Departures: Jun 2026 to Oct 2027
Visit: Indonesia
Exclusive Savings
From
US$2,485
Save 1,065
Per Person
View Trip
8 Day Sailing Greece - Mykonos to Athens with G Adventures
Cruise

8 Days (7 Nights) Mykonos to Athens
Operated By: G Adventures
Departures: Apr 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$1,154
Save 495
Per Person
View Trip
8 Day Montenegro Sailing Adventure from Dubrovnik with Intrepid Travel
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operated By: Intrepid Travel
Departures: Jun 2026 to Oct 2027
Visit: Croatia, Montenegro
Exclusive Savings
From
US$2,083
Save 230
Per Person
View Trip
8 Day Greece Sailing Adventure: Corfu to Kefalonia with Intrepid Travel
Cruise

8 Days (7 Nights) Corfu to Kefalonia
Operated By: Intrepid Travel
Departures: May 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$2,245
Save 588
Per Person
View Trip
14 Day Sri Lanka & Maldives Adventure with G Adventures
Tour + Cruise

14 Days Negombo to Male
Operated By: G Adventures
Departures: Jun 2026 to Dec 2027
Visit: Sri Lanka, Maldives
Exclusive Savings
From
US$2,887
Save 962
Per Person
View Trip
22 Day Sri Lanka in Depth with Maldive Dhoni Cruise (Horton Plains) with Explore Worldwide
Tour + Cruise

22 Days Negombo to Male
Operated By: Explore Worldwide
Departures: Jul 2026 to Nov 2027
Trip Styles: Adventure, Small Group, Sailing
Visit: Sri Lanka, Maldives
From
US$3,260
Per Person
View Trip
10 Day Egypt: Pyramids, Temples & the Nile with G Adventures
New ReleaseRiver Cruise

10 Days Cairo to Cairo
Operated By: G Adventures
Departures: Jun 2026 to Dec 2027
Rivers: Nile
Visit: Egypt
Exclusive Savings
From
US$3,359
Save 1,440
Per Person
View Trip
8 Day Turkey: Sail & Swim with Topdeck
New ReleaseCruise

8 Days (7 Nights) Fethiye to Fethiye
Operated By: Topdeck
Departures: Jun 2026 to Oct 2026
Visit: Turkey
Exclusive Savings
From
US$1,269
Save 80
Per Person
View Trip
9 Day Komodo Island Hopper with TruTravels
New ReleaseTour + Cruise

9 Days Lombok to Labuan Bajo
Operated By: TruTravels
Departures: May 2026 to Nov 2027
Visit: Indonesia
Exclusive Savings
From
US$962
Save 413
Per Person
View Trip
Results: 1-30 of 31

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